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2022 | OriginalPaper | Buchkapitel

Synthesis of N-substituted Maleimides Potential Bactericide

verfasst von : A. C. Trindade, A. F. Uchoa

Erschienen in: XXVII Brazilian Congress on Biomedical Engineering

Verlag: Springer International Publishing

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Abstract

In view of the growing spread of antibiotic resistant bacteria causing high morbidity and mortality, it is essential to develop compounds that are more efficient than those currently on the market. Maleimide derivatives, due to their chemical structure, have biological activity capable of deactivating enzymes and inhibiting the metabolic pathway of these bacteria and fungi. They have high selectivity and are new excellent antimicrobials. In this scenario, the objective of this work was to synthesize, characterize and verify the existence of bactericidal activity of two derivatives of maleimides, 4-vinyl-phenyl-maleimide and Cl-phenyl- maleimide. For this, the structures of the two compounds were characterized by High Resolution Mass Spectrometry (HRMS), Infrared (IR) and Nuclear Magnetic Resonance (NMR) 1H. Both compounds showed a double bond in the maleimide ring, essential for the inhibition of enzymes present in bacteria. The disk diffusion test to determine the bactericidal activity of the compounds, was carried out against the microorganisms: S. Aureus (Staphylococcus Aureus)—Gram positive, Monocytosis Lister—Gram positive, Escherichia Coli Enteropathogenic (EPEC)—Gram negative and Pseudomones Aureginosas—Gram negative. Compounds derived from maleimide obtain greater biological activity in Gram positive microorganisms, as evidenced by the inhibition halo in the diffusion test. The compounds proved to be active in the face of the disk diffusion test, indicating new permeability, selectivity and mechanistic studies, as well as possible applications of them as bactericidal agents.

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Literatur
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9.
Zurück zum Zitat Silvia N, Maria, V (2005) In vitro antifungal properties, structure-activity relationships and studies on the mode of action of N-phenyl, N-aryl, N-phenylalkyl maleimides and related compounds. Arzneim-Forsch 123–132. Silvia N, Maria, V (2005) In vitro antifungal properties, structure-activity relationships and studies on the mode of action of N-phenyl, N-aryl, N-phenylalkyl maleimides and related compounds. Arzneim-Forsch 123–132.
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Zurück zum Zitat Weinstein M, Patel J, Burnham C et al (2018) Performance standards for antimicrobial disk tests. 9th ed. CLSI approved standard M2–A9, Pennsylvania, USA 15–39 Weinstein M, Patel J, Burnham C et al (2018) Performance standards for antimicrobial disk tests. 9th ed. CLSI approved standard M2–A9, Pennsylvania, USA 15–39
Metadaten
Titel
Synthesis of N-substituted Maleimides Potential Bactericide
verfasst von
A. C. Trindade
A. F. Uchoa
Copyright-Jahr
2022
DOI
https://doi.org/10.1007/978-3-030-70601-2_157

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